Mass-spectrometry-directed analysis and purification of pyrrolizidine alkaloidcis/transisomers inGynura japonica

Abstract

Pyrrolizidine alkaloids are highly hepatotoxic natural chemicals that produce irreversible chronic and acute hepatotoxic effects on human beings. Purification of large amounts of pyrrolizidine alkaloids is necessary for toxicity studies. In this study, an efficient method for targeted analysis and purification of pyrrolizidine alkaloid cis/trans isomers from herbal materials was developed for the first time. Targeted analysis of the hepatotoxic pyrrolizidine alkaloids was performed by liquid chromatography with tandem mass spectrometry (precursor ion scan and daughter ion scan), and the purification of pyrrolizidine alkaloids was achieved with a mass-directed auto purification system. The extraction and preparative liquid chromatography conditions were optimized. The developed method was applied to analysis of Gynura japonica (Thunb.) Juel., a herbal medicine traditionally used for detumescence and relieving pain but is potentially hepatotoxic as it contains pyrrolizidine alkaloids. Twelve pyrrolizidine alkaloids (six cis/trans isomer pairs) were identified with reference compounds or characterized by liquid chromatography with tandem mass spectrometry, and five individual pyrrolizidine alkaloids, including (E)-seneciphylline, seneciphylline, integerrimine, senecionine, and seneciphyllinine, were prepared from G. japonica roots with high efficiency. The results of this work provide a new technique for the preparation of large amounts of pyrrolizidine alkaloid reference substances, which will also benefit toxicological studies of pyrrolizidine alkaloids and treatments for pyrrolizidine alkaloid-induced toxicity.

Inhibition of Drp1 protects against senecionine-induced mitochondria-mediated apoptosis in primary hepatocytes and in mice

“…In the present study, we found that Sene, one of the most hepatotoxic common PAs that exists in Senecio vulgaris and Gynura segetum with high contents [29], [30], induced apoptosis in primary cultured mouse and human hepatocytes and in mouse livers. Mechanistically, we found that Sene induced mitochondrial depolarization and fragmentation, release of mitochondrial Cyto c, caspase-3 activation and subsequent apoptosis.…”

Novel immunoassay and rapid immunoaffinity chromatography method for the detection and selective extraction of naringin in Citrus aurantium

“…Additionally, in our previous work, we also separated glycyrrhizic acid from Glycyrrhiza uralensis and resolved 20( S )‐GsRg2 and 20( R )‐GsRg2 using IAC . Other researchers have also reported the application of IAC in the separation of natural products , residual pesticides , and fungal toxin . These studies indicated that the IAC has become an emerging platform for the rapid separation and purification of bioactive constituents from plant extracts and other complex matrices.…”

Targeted and untargeted profiling of alkaloids in herbal extracts using online solid‐phase extraction and high‐resolution mass spectrometry (Q‐Orbitrap)

“…Fig. (a) and (b) shows the MS fragmentation profiles of ALKs that were not previously documented in literature …”

“…1(a) and (b) shows the MS fragmentation profiles of ALKs that were not previously documented in literature. [43][44][45][46][47] Table 3 shows accurate masses of the selected precursor ion and fragments, and the normalised collision energy of the detected targeted (N = 35) and untargeted (49) ALKs.…”